Winter footwear calls for bringing out all your staple ankle boot to kick start a stylish season! Start Fall off on the right foot with a trendy bootie to style for any everyday occasion. Whether paired with a simple and casual wide leg jean or dressed up with a chic patterned midi skirt, there are endless options when it comes to rocking your signature bootie. From dark wash bottoms to bright and bold patterns, there are limitless types of bottoms that can accent a simple bootie perfectly. Here are 11 trendy and fashionable ways to style your ankle boots this winter season!

Flared legs add undeniable retro style to these suave stretch-denim jeans and paired with these staple and simple black ankle booties makes this look perfect for any casual day. We love the power of this look and the freedom it allows for any preferred top!

Topshop Jeans $75

Marc Fisher Boot $189.95


Vibrant zebra stripes embolden a slinky bias-cut skirt that’s begging for a date night. This look is feminine, flirty and perfect for any day you are really trying to serve a stylish fall look! We love these deep brown ankle boots to give the look a bold and commanding presence!

Topshop Skirt $51

Jeffrey Campbell Boot $150

We love the trend of a chic and delicate midi skirt paired with a bold and chunky ankle boot. With a bold print and a long, swingy silhouette, this maxi skirt is sure to be the star of your next OOTD.

Topshop Skirt $43

Sam Edelman Boot $149.95

An abbreviated silhouette modernizes the look of a block-heel Western bootie that’s a stylish addition to your casual look. With this sleek and chic dark bootie, all you need is a trendy dark wash jean to take the look to its most stylish potential!

MOTHER Jeans $228

Lucky Brand Boot $148.95

A wide-legged, cuffed style brings modern edge to these tailored pants that you’ll wear everywhere. Paired with this snakeskin bootie, this look is sure to command any room. This versatile and eye-catching bootie is the perfect addition to these modern, chic and sophisticated pants.

Topshop Pants $34

Marc Fisher Boots $189.95

There’s nothing like elevating a simple and casual denim jean with a clean and chic white bootie! This square toe updates an ultra-sleek bootie and perfectly offsets the casual style of these rigid & hipster jeans!

AG Jeans $98

Sam Edelman Boot $59

Leg-elongating stripes make their flattering mark on these shapely high-waist jeans designed with retro-inspired wide legs. Accent the soft and youthful look of these jeans with a down to earth suede bootie that adds the perfect touch of sophistication and style.

Free People Jeans $118

Marc Fisher Boots $75

Patch pockets and a robust exposed zip give an edgy, utilitarian vibe to wide-leg crop jeans cut from Italian stretch denim in a rich indigo hue. Keep the trendy look alive with these vibrant yet sleek suede booties for a pop of color and confidence.

Cinq A Sept Jeans $295

Botkier $187.95

A skirt to set your inner flower child twirling is made in edgy grey-wash denim that’s finished with a fluttery, frayed hem. Complete the look with a bold bootie styled with angled side seams and a graceful almond toe.

Wash Lab Skirt $128

Blondo Siena Boots $49

Full of chic Western vibes, this nonstretch denim midi is styled with leg-revealing side slits. It’s casual for everyday, yet way more stylish than your oldest pair of jeans. Pair the look with this bold block heel for contemporary-chic sophistication.

Wash Lab Skirt $128

Alva Boot $198.95

10 Trendy Ways to Style Your Ankle Boots This Winter! was last modified: by

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